I recently moved up to the 3" heel from the 2.75" and in this shoe I can barely tell the difference. It is super comfortable, feels stable, and slipped right on. The slipping on part was a LITTLE surprising granted I always order a size down (I wear 7, I''m an 8) but wide. Usually the heel is always a bit tight at first, but for good reason because after a few wears it stretches out and is perfect. I am hoping that these don''t stretch as they fit perfectly already. In conclusion, they don''t wear like the average "Classic" heel, but in ways good so far!